The preparation and evaluation of a new type of chiral oxazaborolane reduction catalyst is proposed. The new approach utilizes a simple and selective one-pot conversion of optically active beta-azido alcohols to these catalysts, a process facilitated by the special reactivity of the 9-borabicyclo[3.3.1]onane(9-BBN) ring system. These catalyst offer potential advantages over existing systems with respect to their ease of preparation, potential versatility and stability. Representatives prochiral ketones will be systematically examined in asymmetric reduction process using borane and these catalysts in both stoichiometric and catalytic amounts to assess the efficacy of these new systems for pharmaceutical and natural product applications.